lilred-
I joined the iPod craze last year (late, mind you!). I got the 8gig iTouch for my all-purpose mp3, video, photo, wifi, personal data organizer use. I sometimes bring it out with me on my solo rides. I just pop it in my rear jersey pocket and away I go... I always keep the music low enough that I can still hear my own bicycle-noise. That keeps it just as safe or safer than driving with your stereo music on in the car. IMO I've never been surprised by a car or passing cyclist with the volume the way I keep it.

I do not ride with it on a group ride though. Even though I think I could still ride safely, the others in a group will immediately judge you and your earbud wire(s). Its just plain rude in a group ride to use one. So... better to just listen to the group huffing n puffing, foul language up hills, etc etc.. Hee hee... I can usually play at least one song just in my head on a group ride. LOL

P.S. No skipping or jumping. The iTouch is the same size as an iPhone. Its a little bulky I guess as iPods go, but it doesn't bother me on rides.